Tag Archives: humiliation

Loser Monday Girls Sleep Wear


girly boy, panty boy, sissificiation, sissy slut, humiliation, mistress, submission






Every sissy slut has that first night of wearing those girly things that their mistress picked out just for them. All of my sluts must get used to wearing girly things to bed each night.  One the first things I do is through out all those ugly boxer shorts and sweat pants.  Then we must go out shopping for something wonderful. This slut and I went to a department store. A really nice elderly lady at first thought we were there for me. Of course that would not do instead my made my slut stand up tall and tell her all the silky things we were purchasing were going in that special chest of drawers. While the old lady could not help but snicker she was happy to help us in every way. The first thing we had to do was find that perfect size. While that waist could be trimmed with a corset and correct exercises a sissy will always be a sissy.  We picked out several night clothes that day. I prefer to break up shopping experiences with serveral trips to draw the humiliation out.  There is something about watching a man slowly turn into a sissy boy.  The first night of wearing these girly things is what breaks down all that resolve.  Humiliation softens a man lets him know that is not in control and makes him want to give himself over to a mistress even more. For a true sissy to find his place he must have his will broken completely down so that he might be rebuilt in a much better girly boy.  When that happens then the true process of transformation can truly occur.  Starting with sleep wear and building from there we will soon make all those nasty male habits disappear and all those girly things come forward.

Looking For A Sissy To Play With

forced feminization gay for pay male cum swallowers male strapon

Push The Button Below To Hear My Voice

I need a sissy to play with someone that is into pretty panties, girly bras, silky hose, sexy shoes and all the other girly things that go with it. Maybe you just like to dress up and feel the fabric against your skin. I have a pretty pink and silver collar to accessories you with when we go out for some exercise. That silver lead fits wonderfully around my wrist and humiliation is the name of the game here. I will always when that game. Maybe you always dreamed of someone making you go out and get a mani and a pedi. Are you the type of girly boy that thinks of sucking cock but would never do it on your own? What ever your sissy fantasy is let’s explore it together. I have played hear and in the ‘real’ world. I know what makes a sissy like you click and I will push you in all the ways you just dream about.

Have you ever thought of forced feminization being made to throw away all your boy things? Having me take you out shopping telling the sales lady that everything we buy is for you? Let’s talk about all those things I will make you buy and wear in your new girlishness.

A good cock sucker knows his place and realizes that for his Goddess he will do anything. If I so chose you will be gay for pay and use that pretty face of your’s for some face fucking . Every penny my gay boy makes is to better my world. My sissy will be the best one giving blow jobs at any party we attend because you always want to make and keep me happy. Be ready to have all your holes wore out. A good slut knows that he is required to be a male cum swallower. When it comes to my toys I have one toy that I enjoy more than any of the others. That toy is my purple 8 inch strap-on while dildos, and anal plugs are nice nothing is better than booty buster. Yes, sometimes I do use it on the girls but male strap-on play is always a fun thing to do. I will get my toy out and just have some fun with your hinny.

Call Me NOW! Give In To Your Pink Side!

Call Diane Callaway for phone sex on Niteflirt.com

Chilly Hicks Living Out Your Fantasies

Role playing is what brings the fun into a good night. It spices everything up and makes for some memorable times. There are so many things that I enjoy doing. We can just talk about all those times I have had sex in a naughty public place. I can always get out my big thick strap-on and show you how to be on the bottom. Are you into a sassy girl that likes to put you in your place and show you complete humiliation no matter where we are? Oh or how about a bunch of guys for me or maybe even for you lets talk about all those fun gang bangs we can explore. I have always liked the thought of caging up a guys cock and me holding the key. I am even into the thought of me in a full chastity belt and you are the only one that can turn me loose. Do you want to be the bad doctor that makes his nurse do all kinds of naughty things in the examining room? We can make it even kinkier where I am the Doctor and all my nurses force you to be our play thing for the afternoon. I am such a bad secretary and you are my high profile boss that knows exactly what it takes to make me behave. Let me be that naughty neighbor that shows off all her goodies and makes you do terrible things would will never share with your wife. Flirty and obnoxious fresh from college show me what an older man does with a young girl like me. There is nothing more important than a good education as your Librarian I am going to make sure you learn your lessons. Even if we have to complete those lessons over and over. College girls like me know how to make a professor do anything and I will make sure you want to reward me with really good grades. You know me when you see me I am a very submissive girl that likes doing kinky things for her dominate male. Put me in my place and I will take complete care of you. Please, Officer I can not get another ticket I am just a girl in trouble if you are bad cop it will end up being a very good night for you. I am habitually late with the rent and there is just no way I can pay this month how naughty of a landlord are you can we work something out? These are just a few little ideas in my deviant mind. Do you have have an idea call me!

Lets talk about all those Roles!

Push The Button Below To Hear My Voice

Call Me Lets Get Naughty

Call ChillyHicks for phone sex on Niteflirt.com

Starting To Dress Up



Some of my guys I have talked to for years. This is one of my sissy guys that ordered some stuff off line.  It depends on the guy but some of them I enjoy making them go out to shop. Not every sissy can handle this because of the level of embarrasment so I have to adjust to personality. It is a lot of fun to shop online together as I generally do not live anywhere near the guys that I play with. I have had a few transgender and crossdressing girlfriends that were close to me. We would always enjoy taking some time and hitting the mall together. Most of the “girl” that I knew where more conservative in dress and most dressed 24/7 so it was all slacks, skirts, bras and panties. The guys on line that just dress for fun time tend to want the more slutty fuck me know look. There is nothing wrong with that and lots of fun to play with but getting fitted for it at the mall by a teenage girl is generally way over whelming.  If you would enjoy showing off some of your outfits send me a picture or two and tell me a little about it in an email. dianecallaway@gmail.com